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Side reaction withN-carboxymethyl amino acids in the synthesis of backbone cyclized peptides (1998)

Besser, Diana ; Greiner, Georg ; Reissmann, Siegmund

Springer

International journal of peptide research and therapeutics 5 (1998), S. 299-303

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ISSN: 1573-3904

Keywords: backbone cyclization ; bradykinin ; branched building units ; diketopiperazine formation

Source: Springer Online Journal Archives 1860-2000

Topics: Chemistry and Pharmacology

Notes: Summary The use ofN-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite thetert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of theN-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF02443547

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